Trump's outlook going from bad to worse

(CNN)-As the White House scans Washington for a bounce-back win after the Obamacare imbroglio, the political forecast is promising only heavy weather.

An unappetizing list of looming congressional showdowns, complex, months-long legislative challenges and intractable threats to President Donald Trump's standing threaten to make the failed health care push look like a small setback.

Approaching sagas of a potential government shutdown, raising the debt ceiling and a moment of truth in the Senate over the potential "nuclear option" confirmation of Supreme Court pick Neil Gorsuch will severely test the political alacrity of a White House already exposed by the busted bid to repeal Obamacare.

The administration is promising aggressive efforts to pass a generational tax reform bill and a bipartisan infrastructure package, though the current Washington environment suggests neither effort will be simple.

Throw in the corrosive impact that the thickening cloud of intrigue over Russia's alleged election meddling is exerting on the White House, and add the challenges posed by the President's own habit of detonating political explosions that damage his own standing, and it's tough to predict the administration's first big political win -- or how much that victory will cost.

"Nobody ever told me that politics was going to be so much fun," Trump declared, perhaps ironically, at a White House reception for senators on Tuesday night.

The challenges facing the new administration are testing enough. But they appear to be compounded by the unorthodox and inexperienced West Wing staff and organizational chaos.

Almost daily, stories seep out of the administration about feuding between top officials and rival centers of power around Trump, including the camp led by political adviser Stephen Bannon and the family inner circle comprising his son-in-law Jared Kushner and his daughter Ivanka Trump, who announced Wednesday she would take an unpaid staff position.

Still, Washington has a habit of writing off presidencies early on if administrations fail to get a fast start. A genuine effort by the Trump team to learn the lessons of its missteps -- and to follow through with the reboot that its public statements suggest is being contemplated -- could improve the odds of getting big things done.

"It is a very challenging environment but I think these guys have been in office for 60 days or whatever, they have never done it before," said Howard Schweitzer, a former Bush administration Treasury official now with Cozen O'Connor Public Strategies. "If they get smarter, they can turn it around."